Prior research has well outlined, detailed, and critiqued the effects of post-colonialism on schooling in Trinidad and Tobago and throughout the Caribbean, but there is a glaring absence of teacher voice regarding its legacy in teaching, learning, and schooling. The literature largely frames teachers as deprofessionalized, invisibilized, passive, or unaware of the historical and political dimensions of schooling. This study explored the logic, relevance, and responsiveness of the instructional climate of a secondary school near Port of Spain, Trinidad. It investigated how teachers at the school believe the Country’s post-colonial context affects their work and how they perceive themselves within that context. Relatedly, the study probed teachers’ conceptions of the role culture and equity play in the classroom and the broader school system. Finally, the study explored teachers’ views on what they perceive as organic, indigenous, and “culturally relevant” practices (broadly defined). Through reporting based on site-based teacher interviews and focus groups, both formal and informal alumni focus groups, copious observational field notes, and critical engagement with an education scholar from the University of the West Indies, this resultant dissertation describes teachers’ candid reflections and strong opinions on these issues as well as a more equitable and critical way forward.